2-(quinolin-2-yl)cyclohexanone | 3311-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(quinolin-2-yl)cyclohexanone
• 英文别名: 2-<2>Chinolyl-cyclohexanon；Cyclohexanone, 2-(2-quinolinyl)-；2-quinolin-2-ylcyclohexan-1-one
• CAS: 3311-56-6
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: GMZXYECITKKOIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(quinolin-2-yl)cyclohexanone 生成 (2E)-2-(1H-quinolin-2-ylidene)cyclohexan-1-one
  参考文献：
  名称：

  GNEENHILL, JOHN V.;LOGHMANI-KHOUZANI, HOSSEIN;MAITLAND, DEREK J., TETRAHEDRON, 44,(1988) N 11, C. 3319-3326

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-2-(1H-quinolin-2-ylidene)cyclohexan-1-one 生成 2-(quinolin-2-yl)cyclohexanone
  参考文献：
  名称：

  GNEENHILL, JOHN V.;LOGHMANI-KHOUZANI, HOSSEIN;MAITLAND, DEREK J., TETRAHEDRON, 44,(1988) N 11, C. 3319-3326

  摘要：

  DOI：

文献信息

• Synthesis of Chiral P,N-ligands derived from Quinoline and their Application in Asymmetric Allylic Alkylations
  作者：Yan-Hong Shen、Hui-Chao Lv、Liang Zhao

  DOI：10.3184/174751911x13082269792294

  日期：2011.6

  Chiral P,N-ligands derived from quinoline and with a trans and cis cyclohexane backbone were easily synthesised in four steps from quinoline N-oxide. The enantiopure trans isomer was obtained by the way of chiral resolution of the mixture of trans- and cis-2-(quinolin-2-yl)cyclohexanol with dibenzoyltartaric acid and then subjected to a Mitsunobu reaction and deprotection to give the corresponding

  从喹啉衍生的具有反式和顺式环己烷主链的手性 P,N-配体可以通过四步从喹啉 N-氧化物轻松合成。反式和顺式-2-(喹啉-2-基)环己醇与二苯甲酰酒石酸的混合物经手性拆分，经光延反应脱保护得到相应的顺式异构体，得到对映体纯反式异构体。光学纯的反式和顺式异构体与氯二苯膦或 PAr2NEt2 反应得到反式和顺式 P,N-配体，它们分别用于不对称烯丙基烷基化，ee 和 ee 分别高达 78% 和 84%。
• 1H NMR Determination of Absolute Configuration of 1- or 2-Aryl-Substituted Alcohols and Amines by Means of Their Diastereomers: Novel Separation Technique of Diastereomeric Derivatives of Pyridyl Alcohols by Extraction
  作者：Masato Matsugi、Kinuyo Itoh、Masatomo Nojima、Yuri Hagimoto、Yasuyuki Kita

  DOI：10.1002/1521-3765(20021216)8:24<5551::aid-chem5551>3.0.co;2-v

  日期：2002.12.16

  A convenient method to determine the absolute configuration of trans-2-aryl cyclohexanols, 1-aryl alcohols and amines was achieved. This method takes advantage of the 1H NMR spectroscopic observations of the remarkable high-field shift of C18-CH3 protons caused by the aromatic shielding effect. It is based on a discrimination of the difference of the environments in two diastereomers derived from 3

  实现了确定反式-2-芳基环己醇，1-芳基醇和胺的绝对构型的简便方法。该方法利用了1H NMR光谱观察到的由芳族屏蔽效应引起的C18-CH3质子显着的高场位移。它基于对衍生自3β-乙酰氧基-5-乙烯酸的两种非对映异构体中环境差异的区分。此外，观察到，基于其碱性的差异，通过萃取简单地分离了吡啶醇的相应的非对映异构衍生物。
• Novel 3,4-diaminoquinoline and pyridine compounds
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0361489A2

  公开（公告）日：1990-04-04

  4-aminopyridine derivatives represented by the general formula: [where R, is a hydrogen atom, a hydroxyl group, a linear or branched lower alkyl group or a cycloalkyl group which may be substituted by a hydroxyl group, a lower alkoxy group, a lower alkyl or a cycloalkyl group which contains a carbonyl group, a morpholino group or a group -NH-B (where B is a lower alkyl group, a cycloalkyl group or a phenyl group); R2 and R3 which may be the same or different each represents a hydrogen atom, a lower alkyl group or a loweralkylcarbonyl group, or when taken together, form an azacycloalkyl group, a morpholino group or an N-methylpiperazinyl group together with the nitrogen atom; R4 and Rs each represents a hydrogen atom, or when taken together with the ring A, form a quinoline ring or a 5,6,7,8-tetrahydroquinoline ring, provided that when each of Ri, R4 and R5 is a hydrogen atom, R2 and R3 are neither a hydrogen atom nor a methyl group at the same time, and when R, is a hydrogen atom and R4 and R5 taken together with the ring A form a quinoline ring, R2 and R3 are neither a hydrogen atom nor an ethyl group at the same time], and an acid addition salts of said 4-aminopyridine derivatives. These compounds are useful as active ingredients in pharmaceutical compositions for improving psychoneural function, especially in the treatment of Alzheimer type dementia and promotion of mnemonic and learning performance.

  由通式表示的 4-氨基吡啶衍生物： [其中 R 是氢原子、羟基、直链或支链低级烷基或环烷基，可被羟基、低级烷氧基、含有羰基的低级烷基或环烷基、吗啉基或-NH-B（其中 B 是低级烷基、环烷基或苯基）取代；R2 和 R3 可以相同或不同，各自代表一个氢原子、一个低级烷基或一个低级烷基羰基，或与氮原子一起形成偶氮环烷基、吗啉基或 N-甲基哌嗪基；R4 和 Rs 各代表一个氢原子，或与环 A 共同形成一个喹啉环或一个 5、6、7、8-四氢喹啉环，条件是当 Ri、R4 和 R5 各为氢原子时，R2 和 R3 既不是氢原子也不是甲基、当 R 为氢原子，且 R4 和 R5 与环 A 形成喹啉环时，R2 和 R3 既不是氢原子，也不是乙基]，以及所述 4-氨基吡啶衍生物的酸加成盐。这些化合物可作为药物组合物的活性成分，用于改善精神神经功能，特别是治疗阿尔茨海默型痴呆症和促进记忆与学习能力。
• Synthesis of 2-(Pyridin-2-yl)phenols and 2-(Pyridin-2-yl)anilines
  作者：Keigo Miki、Katsumi Maeda、Ryosuke Matsubara、Masahiko Hayashi

  DOI：10.1021/acs.joc.4c00423

  日期：2024.4.19

  we report a new synthetic strategy for 2-(pyridin-2-yl)phenols and 2-(pyridin-2-yl)anilines catalyzed by a Pd/C–ethylene system. The starting materials, 2-(pyridin-2-yl)cyclohexan-1-ones, can be easily prepared by the reaction of substituted pyridine N-oxide and cyclohexanones. The most useful feature of this method is that both 2-(pyridin-2-yl)phenols and 2-(pyridin-2-yl)anilines are easily synthesized

  在此，我们报告了一种由 Pd/C-乙烯体系催化的 2-(吡啶-2-基)苯酚和 2-(吡啶-2-基)苯胺的新合成策略。起始原料2-(吡啶-2-基)环己-1-酮可以通过取代的吡啶N-氧化物和环己酮的反应容易地制备。该方法最有用的特点是，2-(吡啶-2-基)苯酚和2-(吡啶-2-基)苯胺都可以使用相同的化合物作为起始材料轻松独立合成，只需添加或不添加氮源。
• Improved Synthesis of Cyclohexane-Backbone Iridium-Complexes of Quinoline-Phosphine and Their Applications in Asymmetric Hydrogenation
  作者：Qibin Liu

  DOI：10.3987/com-20-14284

  日期：——

  The iridium-complexes 3 and 4 with cyclohexane-backbone derived from quinoline were easily synthesized. The key step is cis/trans stereoselective reduction of 2-(quinolin-2-yl)cyclohexanone 5 to trans-2-(quinolin-2-yl)cyclohexanol 6 using Al(Oi-Pr)(3)/i-PrOH and the following diastereomeric optical resolution of racemic 6 using 0.50 equiv (S)-mandelic acid in EtOAc. These complexes were used in the asymmetric hydrogenation of (E)-1,2-diphenylpropene with up to 13% ee/48% cony. using 3 and 35% ee/9% cony. using 4. For the hydrogenation of (2H-chromen-3-yl)methanol, up to 80% ee/95% yield and 72% ee/96% yield were achieved. The same configuration of the products by using 3 and 4 suggested that the absolute configuration was controlled by the configuration of the stereogenic quinolinyl-bearing carbon of the complexes.